Cesium carbonate → tert-Butyl 2-(5-bromo-3-nitropyridin-2-yloxy)acetate

HRID 1628321Notes

Reaction equation

HRID 1628321 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](Cl)=[N:6][CH:7]=1.[OH:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C1C=CN=CC=1.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([O:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 70194125-Bromo-2-chloro-3-nitropyridineHCID 11815394Tert-butyl 2-hydroxyacetate

Product 1

HCID 67497047tert-Butyl 2-(5-bromo-3-nitropyridin-2-yloxy)acetateYield 61.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a flask with 5-bromo-2-chloro-3-nitropyridine (73.B) (800 mg, 3.4 mmol) was added 78.D (mixed with 78.E, 445 mg, 3.4 mmol), cesium carbonate (2.2 g, 6.7 mmol) and N,N-dimethylpyridin-4-amine (82 mg, 0.67 mmol). DMF was used as the solvent. The reaction was heated for 2.5 hours. Standard aqueous workup with EtOAc as solvent and silica gel purification afforded 700 mg of 78.F mixed with some 78.E.

Workup

  1. temperatureThe reaction was heated for 2.5 hours
  2. customStandard aqueous workup with EtOAc as solvent and silica gel purification

Sources & evidence

ORD record
ord-067f9768d4ca430ba0b1444679173dc1
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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